City
Perched at the top of a steep cliff, Pitigliano towers over the hills of Tuscany. Inside the cliff, you will find thousand-year-old caves that house everything from wine shops to garages and shops. And every night the whole city turns red hot.
24 October 20268 min read
Picolo Editorial
24 October 2026
When you are driving from the east, just as you have to brake almost completely to round a sharp hairpin turn, the sight of Pitigliano suddenly reveals itself. At the end of the day, the whole city glows red in the sunset, an effect created by the volcanic bricks made of compressed red sand, which lie bathed in the sun for the last few minutes before it goes down over the vineyards.
It is in the same moment that one understands why the city is known as "little Jerusalem". Towers that stretch towards the sky. Ceramic roof tiles. Row upon row of buildings. Tall houses on top of a vertical cliff. One's associations are not only limited to Israel, but include The Lord of the Rings, The Game of Thrones, and the world of fiction.
Pitigliano is a medieval town on a cliff of tuff stone in the Maremma, in southern Tuscany, in the province of Grosseto. It is known as Little Jerusalem after the Jewish community that lived here for centuries. Stay in Sovana, ten minutes away, or by the hot springs at Saturnia.
Our first choice: Sovana Hotel & Resort, in the neighbouring village ten minutes from Pitigliano. Check availability and prices at Sovana Hotel & Resort
That the city was sacred was probably exactly what the Jews who fled Lazio and Rome thought five centuries ago. Or rather hoped. Driven out of the holy city by brute force, the refugees fled here to the southern tip of Tuscany. And maybe they rounded exactly the same bend, thinking that here in this red city they could establish a Jewish enclave and a synagogue, a synagogue that today is the only one in this part of Italy.
Little Jerusalem still appears very suddenly today. Although the city is situated on a steep cliff, it does not sit at a high elevation, and Pitigliano is not visible until you are just a few turns away. After miles of endless hills and rows of vines, the city is suddenly there. Without warning.
Just be careful you don't collide with the car in front.
Many people stop abruptly in the middle of the narrow road, pick up their phones and point their lenses at the city's impressive skyline to the east.
Find exclusive deals with our partners: Book your stay in Italy here.
There are endless narrow alleys, stairs and cobbled streets in all directions. It's almost impossible not to get lost.
To enter the city itself, you must cross a deep river valley and then follow the sharp turns up to the city gate and into the oldest part of Pitigliano, which has 3,000 years of history behind it.
The streets of Pitigliano are narrow. Very narrow. Very few of them can be navigated by car. The city's largest intersection consists of another almost impossible hairpin turn, which is the subject of a cacophony of chaos from morning to late evening. Those who are not familiar with the small town are not aware that one must go all the way to the opposite lane to get through the hairpin turn, and this lack of local knowledge creates an almost insoluble traffic jam. And one naturally hesitates to drive on the wrong side of the road in a country like Italy.
Once it is safely parked, preferably in the newer part of the city, you can explore the old town of Pitigliano for days on foot. There are endless narrow alleys, stairs and cobbled streets in all directions. It's almost impossible not to get lost. Charming shops and restaurants have found their home in the ancient brick buildings. The oldest houses still standing dates back to the 1100s. The city also has another nickname: Citta del tufo. Named after the aforementioned bricks:tufo: made from red volcanic sand.
Find exclusive deals with our partners: Book your stay in Italy here.
A small luxury hotel in a historic palazzo directly opposite the Colosseum. Ask for a room with a view, and book a table at Aroma on the roof, which looks straight onto the amphitheatre.
Hotels.com (Expedia Group)With its 3,800 inhabitants, Pitigliano is not a large city, nor can it be called a typical tourist trap. The city is proud of its unique traditions and has to a greater extent than many others preserved its culture and identity: cut off from more trafficked parts of Italy. Many of the employees in the city's 14-15 restaurants do not speak English, the menus are often in Italian only, and frequently consist of traditional Italian dishes such as lardo (a type of salumi) and stinco (pork skank). But of course, far more familiar dishes such as pizza and pici al ragu are also on offer.
Read more: Civita di Bagnoregio: the dying city clinging to the cliffs
On the whole, Pitigliano feels very Italian and genuine. This also applies to the restaurant Il Caveau, which is literally located in the middle of the city walls. In addition to being one of the city's best restaurants, it also has the best views. Remember to book a table on the terrace well in advance. You will find the restaurant after a fun stroll through some of the very narrowest alleys.
The well-known winemaker Tommasi owns and manages many of the vineyards and farms that surround the clifftop town. On the way into town, the wine house has its own wine shop in a charming cave by the road. But you will of course also wish to taste also the products offered by small, local producers as well. Like many Italian cities, Pitigliano has its own cooperative for the production and sale of wine. For over fifty years, Cantina Sociale di Pitigliano has delivered award-winning wines such as Bianco di Pitigliano DOC and Rosso Sovana DOC. These local gems can also be found in most restaurants and wine shops.
One experience that's easy to miss if you don't know about it is the hidden Parco Orsini. In this park, you can wander through thousands of years of history. If you find the right staircase, which is difficult enough in itself in the labyrinths of Pitigliano, you can stroll alongside waterfalls, cliffside woods and caves, and monuments and statues for hours. The park has been nicknamed Parco degli Strozzoni, "the park of the strangler". In 1575, Count Orsini was accused of strangling his wife and throwing her off a bridge. According to written sources, the count became immensely unpopular after the murder and was himself killed on the same bridge the following year.
You can look out over the city walls from almost everywhere in the city and experience views of waterfalls, the river valley, and the surrounding vineyards. On the outside of the walls, you can also walk on an airy bridge, at the very highest point of the cliffs. If you can find it, that is. As with so much else, you often have to make a few wrong turns before you find your way. And it is far from certain that the employees of the restaurants are able to show you the right way. It's almost like the attractions aren't intended to be easy to find, forcing you into a journey of discovery.
Many combine a visit to Pitigliano with a visit to another rock town. Civita di Bagnoregio, also called La città che muore, "the dying city", is an hour's drive away, just to the east. Just like Pitigliano, the town is perched on top of a steep cliff. But unlike Pitigliano, Bagnoregio is very hard hit by erosion, earthquakes and landslides. Over hundreds of years, more and more of the city has eroded and gradually disappeared. Efforts have been made to save the city from further destruction through reinforcement and other steps, so that its 14 residents remaining can continue to live there. If you are in this part of Tuscany, a trip to Bagnoregio is highly recommended. Go now, before it's too late!
As many know, Italy is well known for its volcanic activity. Not far from Pitigliano, a hot spring emerges from the earth's interior. Saturnia houses both golf courses and spa facilities, but the hot spring itself is open and free to everyone. Saturnia is like a light blue river that cascades out of the ground and flows down into natural pools, which the water has created over thousands of years. For some, it may be an unfamiliar experience to bathe in the 40-degree Celsius sulfurous water when there is roughly the same temperature in the air. For Italians, Saturnia is a very popular destination, which is also said to have a healing effect on a wide variety of physical ailments.
Pitigliano is not located on the busiest route and is some distance away from the most famous cities in Tuscany. It is about two hours by car from Rome and almost equally far from Sienna in the north (Sienna, incidentally, is Pitigliano's oldest enemy and the two cities were continuously at war in the Middle Ages).
The easiest way to get there is to rent a car in Rome or Florence. If you want to combine Pitigliano with swimming, it is about an hour's drive to the fantastic and endless beaches of Grosseto, or you can get to Bolsena Lake in half the time. Bolsena is widely known for its crystal-clear water. There is no train station in the immediate vicinity of Pitigliano.
Great hotels in Rome
A private mansion in Rione Campo Marzio, a few minutes from the Spanish Steps, now a hotel in The Leading Hotels of the World. Most of central Rome is within walking distance.
Photo: PicoloFor hotels inside Pitigliano, in Sovana and by the hot springs at Saturnia, see our guide to Pitigliano: Vie Cave, wine and hotels.
Pitigliano earned the nickname Little Jerusalem because of its long Jewish history. Around five centuries ago, Jews driven out of Rome and Lazio came here and established a ghetto and a synagogue, which today is the only one in this part of Italy.
The town is built of volcanic stone made from compressed red sand. In the last minutes before the sun sets over the vineyards, the stone faces the sun directly and the whole town glows red. The best view is from the road in from the south.
Pitigliano sits on a sheer cliff in southern Tuscany. It is not high up in the landscape and appears suddenly after a sharp bend when you arrive from the east. Inside the cliff are thousand-year-old caves housing wine shops and stores.
